Iodobenzene → HCID 22254453, compound

HRID 433994Notes

Reaction equation

HRID 433994 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][O:20][CH2:21][C:22]#[CH:23])[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1.I[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH3:1][O:2][CH2:3][CH2:4][C:5]1[N:6]([CH2:18][CH2:19][O:20][CH2:21][C:22]#[C:23][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:7]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:17]=1

Participants

3

Reactant 2

HCID 11575IodobenzeneHCID 22254467HCID 22254467, compound

Product 1

HCID 22254453HCID 22254453, compoundYield 346.4%

Procedure

Using the general method of Example 12 Part A, 2-(methoxyethyl)-1-[2-(prop-2-ynyloxy)ethyl]-1H-imidazo[4,5-c]quinoline (2.72 g, 1.79 mmol) was reacted with iodobenzene (1.1 mL, 9.67 mmol) at ambient temperature. After 45 minutes the reaction was judged complete. The volatiles were removed under reduced pressure and the resulting oil partitioned between dichloromethane and 5% aqueous sodium bicarbonate. The aqueous layer was extracted with dichloromethane. The organic fractions were combined, washed with brine, dried with anhydrous sodium sulfate, and then concentrated under reduced pressure to leave a brown solid. The solid was purified by chromatography over silica gel (95/5 (dichloromethane/methanol) and trituration with hexane to provide 2.39 g of 2-(methoxyethyl)-1-{2-[(3-phenylprop-2-ynyl)oxy]ethyl}-1H-imidazo[4,5-c]quinoline as a yellow solid.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customthe resulting oil partitioned between dichloromethane and 5% aqueous sodium bicarbonate
  3. extractionThe aqueous layer was extracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto leave a brown solid
  8. customThe solid was purified by chromatography over silica gel (95/5 (dichloromethane/methanol) and trituration with hexane

Sources & evidence

ORD record
ord-36a899ac9bbb410cbafc69e633854d0f
Source dataset
uspto-grants-2003_12
Patent number
US06670372B2

Reaction notes

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